EP0542381A3 - Optically active compounds - Google Patents

Optically active compounds Download PDF

Info

Publication number
EP0542381A3
EP0542381A3 EP19920203667 EP92203667A EP0542381A3 EP 0542381 A3 EP0542381 A3 EP 0542381A3 EP 19920203667 EP19920203667 EP 19920203667 EP 92203667 A EP92203667 A EP 92203667A EP 0542381 A3 EP0542381 A3 EP 0542381A3
Authority
EP
European Patent Office
Prior art keywords
optically active
active compounds
naphthylene
group
pyridazinylene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19920203667
Other languages
German (de)
French (fr)
Other versions
EP0542381A2 (en
Inventor
Masahiro Satoh
Kunikiyo Yoshio
Tetsuya Watanabe
Hiroshi Kishiki
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanyo Chemical Industries Ltd
Original Assignee
Sanyo Chemical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP1047948A external-priority patent/JPH0729966B2/en
Priority claimed from JP1047949A external-priority patent/JPH03115243A/en
Priority claimed from JP1049469A external-priority patent/JPH02229174A/en
Priority claimed from JP1049468A external-priority patent/JPH02229128A/en
Priority claimed from JP1192061A external-priority patent/JPH0356445A/en
Priority claimed from JP1299928A external-priority patent/JPH03161473A/en
Priority claimed from JP1303851A external-priority patent/JP2608789B2/en
Application filed by Sanyo Chemical Industries Ltd filed Critical Sanyo Chemical Industries Ltd
Publication of EP0542381A2 publication Critical patent/EP0542381A2/en
Publication of EP0542381A3 publication Critical patent/EP0542381A3/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/58—Dopants or charge transfer agents
    • C09K19/586—Optically active dopants; chiral dopants
    • C09K19/588—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/33—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/17—Unsaturated ethers containing halogen
    • C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/17—Unsaturated ethers containing halogen
    • C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
    • C07C43/176—Unsaturated ethers containing halogen containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K19/126—Compounds containing at least one asymmetric carbon atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/58—Dopants or charge transfer agents
    • C09K19/586—Optically active dopants; chiral dopants

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal Substances (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Optically active compounds represented by the following formula are disclosed:
wherein R and R' are C₁₋₂₀ alkyl groups; X and Y₁ are -, O, S or divalent groups such as COO, OOC, and OCOO; A₁ is a cyclic group such as 1,4-phenylene, 2,5-pyridylene, 2,5-pyrimidinylene, 3-6-pyridazinylene, 2,5-pyrazinylene, 2,6-naphthylene and/or 4,4'-biphenylene, and Nt is à 2,6-naphthylene group.
EP19920203667 1989-02-27 1990-02-26 Optically active compounds Withdrawn EP0542381A3 (en)

Applications Claiming Priority (16)

Application Number Priority Date Filing Date Title
JP1047948A JPH0729966B2 (en) 1989-02-27 1989-02-27 Optically active compound
JP47949/89 1989-02-27
JP47948/89 1989-02-27
JP1047949A JPH03115243A (en) 1989-02-27 1989-02-27 Optically active compound
JP49470/89 1989-03-01
JP49468/89 1989-03-01
JP1049469A JPH02229174A (en) 1989-03-01 1989-03-01 Optically active compound
JP1049468A JPH02229128A (en) 1989-03-01 1989-03-01 Optically active compound
JP49469/89 1989-03-01
JP4947089 1989-03-01
JP192061/89 1989-07-25
JP1192061A JPH0356445A (en) 1989-07-25 1989-07-25 Optically active compound
JP1299928A JPH03161473A (en) 1989-11-17 1989-11-17 Optically active compound
JP299928/89 1989-11-17
JP303851/89 1989-11-22
JP1303851A JP2608789B2 (en) 1989-03-01 1989-11-22 Optically active compound

Related Parent Applications (2)

Application Number Title Priority Date Filing Date
EP90302013.9 Division 1990-02-26
EP90302013A Division EP0385692B1 (en) 1989-02-27 1990-02-26 Optcally active compounds

Publications (2)

Publication Number Publication Date
EP0542381A2 EP0542381A2 (en) 1993-05-19
EP0542381A3 true EP0542381A3 (en) 1993-06-02

Family

ID=27572360

Family Applications (2)

Application Number Title Priority Date Filing Date
EP90302013A Expired - Lifetime EP0385692B1 (en) 1989-02-27 1990-02-26 Optcally active compounds
EP19920203667 Withdrawn EP0542381A3 (en) 1989-02-27 1990-02-26 Optically active compounds

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP90302013A Expired - Lifetime EP0385692B1 (en) 1989-02-27 1990-02-26 Optcally active compounds

Country Status (3)

Country Link
US (2) US5160662A (en)
EP (2) EP0385692B1 (en)
DE (1) DE69003709T2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2022880A1 (en) * 1989-08-18 1991-02-19 Toyozi Shimizu Carboxylate compounds, liquid crystal compositions containing said compounds and liquid crystal element
JP2872372B2 (en) * 1990-09-04 1999-03-17 キヤノン株式会社 Liquid crystal compound, liquid crystal composition containing the same, and liquid crystal device using the same
JP3262170B2 (en) * 1990-11-27 2002-03-04 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング 3,6-disubstituted 2-halopyridine compounds
EP0518636A1 (en) * 1991-06-11 1992-12-16 Sanyo Chemical Industries Ltd. Liquid crystal compounds and compositions
JP3487613B2 (en) * 1992-07-24 2004-01-19 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング Chiral 2,6-difluorobenzene derivative
US5770108A (en) * 1995-06-28 1998-06-23 Mitsui Toatsu Chemicals, Inc. Pyrimidine compound and liquid crystal composition and liquid crystal element using the same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987005018A2 (en) * 1986-02-17 1987-08-27 MERCK Patent Gesellschaft mit beschränkter Haftung Optically active compounds
EP0294852A2 (en) * 1987-06-12 1988-12-14 Canon Kabushiki Kaisha Ferroelectric liquid crystal device

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4613209A (en) * 1982-03-23 1986-09-23 At&T Bell Laboratories Smectic liquid crystals
DE3377219D1 (en) * 1982-11-26 1988-08-04 Hitachi Ltd Smectic liquid crystal compounds and liquid crystal compositions
JPS62169883A (en) * 1985-10-30 1987-07-27 Canon Inc Liquid crystal element
JP2562606B2 (en) * 1986-09-08 1996-12-11 ダイセル化学工業株式会社 Optically active compound
EP0293910B1 (en) * 1987-06-04 1994-02-02 Canon Kabushiki Kaisha Liquid crystal composition and liquid crystal device containing same
DE3812191A1 (en) * 1988-04-13 1989-10-26 Merck Patent Gmbh CHIRAL OR ACHIRREL RING LINKS
JPH02169883A (en) * 1988-12-21 1990-06-29 Toyoda Mach Works Ltd Vane pump

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987005018A2 (en) * 1986-02-17 1987-08-27 MERCK Patent Gesellschaft mit beschränkter Haftung Optically active compounds
EP0294852A2 (en) * 1987-06-12 1988-12-14 Canon Kabushiki Kaisha Ferroelectric liquid crystal device

Also Published As

Publication number Publication date
DE69003709D1 (en) 1993-11-11
EP0385692B1 (en) 1993-10-06
EP0385692A3 (en) 1991-10-30
DE69003709T2 (en) 1994-03-10
US5160662A (en) 1992-11-03
EP0385692A2 (en) 1990-09-05
EP0542381A2 (en) 1993-05-19
US5290478A (en) 1994-03-01

Similar Documents

Publication Publication Date Title
EP0396937A3 (en) 3-substituted polypyrrole
TW283161B (en)
EP0379677A3 (en) Silicone surfactants
EP0369262A3 (en) Novel pyrroles
IL95946A0 (en) Preparation of tetrabromo-4,4'-alkylidenediphenols
EP0542381A3 (en) Optically active compounds
AR245944A1 (en) Polysiloxanes with pendant sterically hindered phenol moiety connected to the silicon atom via a carbonyloxy-containing link
EP0532915A3 (en) Phosphoinositolglycan-peptide with insulin like activity
EG18437A (en) Insecticidal n-substituted-n'-substituted-n,n'-diacylhydrazines
EP0377209A3 (en) Improved silicone surfactants
EP0356963A3 (en) Novel siloxane compounds terminated with a diol at one end thereof
EP0381005A3 (en) Ocular lens material
KR960014775B1 (en) Emulsified hair cosmetic
EP0295679A3 (en) Physiologically-active novel peptides
CA2010411A1 (en) Carbon-fiber-reinforced polyimide resin compositions
EP0399358A3 (en) Butenoic acid derivatives
EP0374716A3 (en) Modified polyarylate resin and composition comprising the same
EP0381235A3 (en) Pyrrolidine compound and pharmaceutical use
EP0372299A3 (en) Polycarbonate cross-linker resin and fire resistant compositions made therefrom
EP0305059A3 (en) Organosilicon compounds their preparation and use
IL100386A0 (en) Cell free marek's disease virus vaccine
JPS5584417A (en) Copolyamide fiber
PL298495A1 (en) Novel derivatives of 7-ethynyl-alpha-/methoxymethylene/-1-naphtalenoacetic acids and method of obtaining same and their application as pesticides
EP0388124A3 (en) Wholly aromatic polyester and composition containing the same
JPS5584323A (en) Copolyamide containing aromatic oligoamide unit and preparation thereof

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AC Divisional application: reference to earlier application

Ref document number: 385692

Country of ref document: EP

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): CH DE FR GB IT LI NL

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): CH DE FR GB IT LI NL

17P Request for examination filed

Effective date: 19930707

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Withdrawal date: 19940608